Why do you want to move? To experience a more urban way of life, to be closer to our ski condo, to be surrounded by people who are more active, to experience way better work opportunities (D absolutely, Me -- Jury is still out).
Are you dissatisfied with your life as it currently stands? Yes and No. Yes with respect to environment and peers. No with respect to finances and how our life generally feels like and looks like on paper. It would be easier in some ways if we had to move because of need. As it is, we live a pretty diversified life right now. It isn't "perfect" but we feel we've made the most of what we have. For sure the topic of whether it is an ungratefulness issue has come up and we don't feel it is that at all. Being that it is a bit too steep effort wise to try for an oversea move, within Canada is our best shot at something different.
Why would you even consider such an "expensive" place? Bigger city means far more activities to chose from. We are thinking of how we want to continue living beyond work. Remember how difficult it was for me to find a private ballet teacher? No problem where we are looking. Plus there is an opportunity to learn something I've always wanted to do -- Biathlon!!! -- and other things we want to get into, like adventure racing. The terrain and culture out west is totally conducive to that. There are less expensive places out west but unfortunately that also tends to mean not great work opportunities for D whereas better for me work wise, for a number of reasons. Finding a place that is ideal for both of us has been tough.
Why Now? Timing is good with respect to us probably having another 10 years or so left in our careers. Long enough to build something meaningful (more relevant for me). Honestly, since I've moved to part time, I've been more content than I can remember (am also a creature of habit). D's spear heading this search but I'm open to new opportunities and definitely open to a more exciting life. Feeling like we've "beat" the system here in Ontario, allowing us to be in a place financially where we can afford to dream "bigger" or so we think. Mind you, out there we're not swimming in a small pond anymore.
What would you have to give up? The cottage, our large well built and architecturally significant home, significant square footage, possibly a garage, a car (a good thing), possessions (not necessarily a bad thing, but it might mean my piano and French antiques), convenient flights to Europe (this move would add another 4+ hours one way), my autonomy at work (biggie -- not at all sure about having to work "under" someone again), a short commute (me), Pearson Airport (it's not perfect but we like it), The Great Lakes (We are spoiled in Ontario with abundance of fresh water. Small lakes just aren't the same.), good friends (lucky I'm not adverse to travelling, don't see this as much of an issue, am good with keeping in touch).
How would you make it work? Bigger city, higher percentage of financially leverage lives -- Not a place we wish to venture into. No way would I consider buying a house for 600K+ at this stage of my/our lives. I don't want to sink that much money in what could/would be our "final home". Don't people tend to go the other way and sell to get money out of their home? We are looking for the least expensive (if it even exists) reasonable form of housing. What that means is just being there has to be so great that we would be willing to give up house ownership. I'm getting ahead of myself again. We would be renting for the first year until we get to know our way around. I can see us moving to a different neighbourhood the following year and seeing how we like it. If we pare down our possessions, it shouldn't be problem. I've already found a storage place just in case.
What are you afraid of? Of failing. Of giving up everything we have here and realizing too late and not having anything to come back to (thinking of my office here because I would have sold it). Of feeling "poor" and finding we have to work harder than predicted and not having the amount of leisure time we thought we'd have. Of all the work involved. Of feeling claustrophobic. Of being dependent on D until I find the right fit.